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Issue 3, 2009
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Kinetic and thermodynamic control in the stereoselective formation of trans- and cis-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones

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Abstract

A range of ferrocenylimines derived from ferrocenecarboxaldehyde and the α-amino acids (S)-alanine, (S)-2-aminobutyric acid, (S)-norvaline, (R)-2-phenylglycine, (S)-phenylalanine, O-benzyl (S)-serine, and (S)-tryptophan can be cyclised stereoselectively to afford either the corresponding cis- or trans-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones. The cyclisation reaction shows marked temperature dependence, giving rise preferentially to the trans-oxazolidinone under kinetic control (−78 °C) and the thermodynamic cis-oxazolidinone at −15 °C to rt.

Graphical abstract: Kinetic and thermodynamic control in the stereoselective formation of trans- and cis-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones

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Publication details

The article was received on 19 Aug 2008, accepted on 22 Sep 2008 and first published on 04 Dec 2008


Article type: Paper
DOI: 10.1039/B814450H
Citation: Org. Biomol. Chem., 2009,7, 518-526
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    Kinetic and thermodynamic control in the stereoselective formation of trans- and cis-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones

    F. Alonso, S. G. Davies, A. S. Elend and A. D. Smith, Org. Biomol. Chem., 2009, 7, 518
    DOI: 10.1039/B814450H

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